4-(2-oxo-2-phenylethyl)chroman-2-one | 112217-97-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4-(2-oxo-2-phenylethyl)chroman-2-one
• 英文别名: 2-oxo-4-phenacylchroman；4-Phenacyl-chroman-2-one；4-phenacyl-3,4-dihydrochromen-2-one
• CAS: 112217-97-7
• 化学式: C₁₇H₁₄O₃
• 分子量: 266.296
• InChiKey: FLRIOMDNGFPPHU-UHFFFAOYSA-N

物化性质

• 沸点：
  407.1±24.0 °C(Predicted)
• 密度：
  1.206±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  Iodo-acetic acid 2-((E)-3-oxo-3-phenyl-propenyl)-phenyl ester 在 碘代三甲硅烷 作用下， 以 乙腈 为溶剂， 反应 3.0h， 以100%的产率得到4-(2-oxo-2-phenylethyl)chroman-2-one
  参考文献：
  名称：

  A δ-lactone synthesis involving an intramolecular 1,4-addition of α-iodoacetates to enones

  摘要：

  DOI：

  10.1016/s0040-4039(00)85267-3

文献信息

• Facile synthesis of 4-substituted 3,4-dihydrocoumarins via an organocatalytic double decarboxylation process
  作者：Shiyong Peng、Lei Wang、Haibing Guo、Shaofa Sun、Jian Wang

  DOI：10.1039/c2ob25075f

  日期：——

  building blocks, have attracted considerable attention due to their various biological activities. Herein, we have documented an efficient and convenient double decarboxylation process for the synthesis of 4-substituted 3,4-dihydrocoumarin in moderate to excellent yields under mild reaction conditions (up to 98%).

  3,4-二氢香豆素被认为是有价值的组成部分，由于其各种生物活性而引起了相当大的关注。在本文中，我们已经记录了在温和的反应条件下（高达98％）以中等至极好的收率合成4-取代的3,4-二氢香豆素的高效便捷的双脱羧方法。
• NHC-Catalyzed Reactions of Aryloxyacetaldehydes: A Domino Elimination/Conjugate Addition/Acylation Process for the Synthesis of Substituted Coumarins
  作者：Eric M. Phillips、Manabu Wadamoto、Howard S. Roth、Andrew W. Ott、Karl A. Scheidt

  DOI：10.1021/ol802448c

  日期：2009.1.1

  N-Heterocyclic carbenes (NHCs) catalyze a domino Michael addition/acylation reaction to form 3,4 through addition of the NHC to an aryloxyaldehyde followed by elimination of a phenoxide leaving group, generating an enol intermediate. This transient nucleophile generated in situ performs a 1,4-addition onto a conjugate acceptor, and the carbene catalyst Is regenerated upon acylation of the phenoxide anion resulting in formation of 3,4-dihydrocoumarins.
• Bojilova, Anka; Ivanov, Christo, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1987, vol. 26, # 1-12, p. 731 - 735
  作者：Bojilova, Anka、Ivanov, Christo

  DOI：——

  日期：——
• BOJILOVA, ANKA;IVANOV, CHRISTO, INDIAN J. CHEM., 26,(1987) N 8, 731-735
  作者：BOJILOVA, ANKA、IVANOV, CHRISTO

  DOI：——

  日期：——
• Enantioselective Formation of Substituted 3,4-Dihydrocoumarins by a Multicatalytic One-Pot Process
  作者：Christian Borch Jacobsen、Łukasz Albrecht、Jonas Udmark、Karl Anker Jørgensen

  DOI：10.1021/ol302627u

  日期：2012.11.2

  The formation of optically active 3,4-dihydrocoumarins is presented by merging aminocatalysis with an N-heterocyclic carbene-catalyzed internal redox reaction. The products are formed in good to excellent yields and in general with excellent enantioselectivities. Moreover, the developed procedure demonstrates the potential of enantioselective, multicatalytic sequences. By employing an enantiopure aminocatalyst in the enantiodifferentiating step, the challenges related to achieving high stereoinductions by deployment of optically active NHC-catalysts can be circumvented.